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Green Synthesis of (S)-5,5′-diamino-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl |
YUE Chuan-jun, ZHAO Zi-biao, SU Yang, LIU Bao-liang |
School of Science, Changzhou Institute of Technology, Changzhou 213022, China |
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Abstract (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl dioxide[(S)-2] was obtained by oxidation, using H2O2 as the oxidant and (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl[(S)-1] as the starting material. (S)-5,5′-dinitro-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl dioxide[(S)-3] was obtained by nitration of (S)-2 catalyzed by acidic resin. (S)-5,5′-diamino-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl dioxide[(S)-4] was obtained by hydrogenation reduction of [(S)-3] catalyzed by Pd/C. (S)-5,5′-diamino-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl was synthesized by reduction of (S)-4 catalyzed by HSiCl3/PPh3. The total yield was 65.6%. The structures were confirmed by 1H NMR, 31P NMR and IR.
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Received: 27 October 2014
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